Acetaldehyde → HCID 70049907, compound

HRID 1110463Notes

Reaction equation

HRID 1110463 reaction equation
C([BH3-])#N.[Na+].[C:5]([O:9][C:10](=[O:59])[C@H:11]([CH2:47][C:48]1[CH:53]=[CH:52][C:51]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[CH:50][CH:49]=1)[NH:12][C:13]([C:15]1([CH2:20][C@H:21]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:22][NH:23][C:24](=[O:39])[C@H:25]([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH2:26])[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])([CH3:8])([CH3:7])[CH3:6].[CH:60](=O)[CH3:61].Cl>C(O)C>[C:5]([O:9][C:10](=[O:59])[C@H:11]([CH2:47][C:48]1[CH:49]=[CH:50][C:51]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[CH:52][CH:53]=1)[NH:12][C:13]([C:15]1([CH2:20][C@H:21]([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[CH2:22][NH:23][C:24](=[O:39])[C@H:25]([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[NH:26][CH2:60][CH3:61])[CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:14])([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 53998816HCID 53998816, compound

Product 1

HCID 70049907HCID 70049907, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium cyanoborohydride (45 mg) was added in one portion to a stirred, ice cold solution of N-{1-[2-(S)-t-butyloxycarbonyl-3(N6 -t-butyloxycarbonyl-(S)-lysylamino)propyl]-1-cyclopentanecarbonyl}O-t-butyl-(S)-tyrosine-t-butyl ester (507 mg) and acetaldehyde (31 mg) in aqueous ethanol (80%, 10 ml) and the pH adjusted to 5 with 1N hydrochloric acid. The resulting solution was allowed to warm to room temperature and stirred for 1.5 hours. The reaction mixture was evaporated to dryness and the residue partitioned between water and ethyl acetate. The phases were separated and the organic phase washed with a little aqueous sodium bicarbonate, dried (MgSO4), filtered and evaporated. The residue was chromatographed over silica gel, eluting with mixtures of hexane and ethyl acetate containing 1% diethylamine to yield the title compound as an oil (370 mg, 64%) Rf 0.55 (silica; CH2Cl2, CH3OH, NH4OH; 90:10:1).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase washed with a little aqueous sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed over silica gel
  9. washeluting with mixtures of hexane and ethyl acetate containing 1% diethylamine

Sources & evidence

ORD record
ord-bd9ef9ff31b64d4bb56e0f9bdbd9d082
Source dataset
uspto-grants-1990_12
Patent number
US04975444

Reaction notes

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